(historical) A period that lasted from the mid-16th (or mid-15th) to the mid-19th centuries, in which the dominance of sailing ships in global trade and warfare culminated.

Alternative form of that ship has sailed

(obsolete, nautical) To act in an unusual manner; to behave differently.

(nautical) To sail in a direction close to that from which the wind is blowing, but still making headway / (idiomatic) To behave in a manner that is on the verge of being dangerous, improper or illegal

(nautical) A triangular sail carried on a boat's mast.

plural of shoulder-of-mutton sail

(nautical) To adjust a ship's sails to make the best of wind conditions.

(obsolete, nautical, idiomatic) To deceive or intentionally mystify.

(idiomatic) To discourage someone greatly; to cause someone to lose hope or the will to continue; to thwart or minimize someone's ambitions.

Alternative form of take the wind out of someone's sails